You won't find skydiving at WDW, but if you have a car and are willing to travel I'm sure there are places within a reasonable distance. Not sure how far Deland is from WDW, but they had lots of skydiving at one point in history.
MG was correct that there is no skydiving at WDW. A close second might be parasailing from the marina at the Contemporary Resort. The company that runs the parasailing is Sammy Duvall's Water Sports. The operate daily weather permitting.